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11. This result would be supported by the 13C NMR chemical shifts of 3a
(d 179.59 (q, J¼34 Hz)) and 3e (d 197.94), clearly indicating more
deshielded circumstance of the carbonyl carbon atom of 3e, see: Asao,
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5. When ethyl trichloroacetate was added to an ethereal solution of PhMgBr
(4 equiv) at 0 ꢀC and then refluxing for 1.5 h furnished an almost quanti-
tative amount of PhCl, see: Kaluszyner, A.; Reuter, S. J. Am. Chem. Soc.
1953, 75, 5126.
6. In Ref. 2, Creary reported basically identical result for the reaction of
PhMgBr and ethyl acetate in ether at ꢁ78 ꢀC, followed by warming to
rt leading to the exclusive formation of the tertiary alcohol 1,1-diphenyl-
ethanol in 96% yield.
7. For the MPV reductions using fluorine-containing substrates, see:
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13. A small amount of the aldol product (ca. 5% yield) was also detected in
the case of trifluorinated case. The similar situation was occurred for the
related system in Ref. 7b.
14. Wu, Y.-D.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 906.
15. Imaginary frequencies for these TSs were obtained as ꢁ201.28 cmꢁ1 for
13a and ꢁ525.17 cmꢁ1 for 13e.
8. Although this yield should be theoretically zero, a small amount of con-
taminant might cause this reaction.
16. Very recently, the similar type of reaction was appeared using a combina-
tion of RfMgBr and Ti(Oi-Pr)4, see: Mikami, K.; Murase, T.; Itoh, Y.
J. Am. Chem. Soc. 2007, 129, 11686. Moreover, Oppenauer oxidation
by using the high electrophilicity of trifluoroacetone was also reported.
9. Computation was carried out by Gaussian 03W using B3LYP/
6-311þþG** (except for the TS 13 as well as the substrates and products
(11 and 12) in Figure 1 using B3LYP/6-31þG*) level of theory. Frisch,
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J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi,
´
Mello, R.; Martınez-Ferrer, J.; Asensio, G.; Gonzalez-Nunez, M. E.
J. Org. Chem. 2007, 72, 9376.
´
´~
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